CN106521970A - Method for preparing polythioether polymer grafted carbon fibers on basis of thiol-ene photopolymerization - Google Patents

Method for preparing polythioether polymer grafted carbon fibers on basis of thiol-ene photopolymerization Download PDF

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CN106521970A
CN106521970A CN201610965271.XA CN201610965271A CN106521970A CN 106521970 A CN106521970 A CN 106521970A CN 201610965271 A CN201610965271 A CN 201610965271A CN 106521970 A CN106521970 A CN 106521970A
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carbon fibers
carbon fiber
grafted
sulfydryl
mole
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CN106521970B (en
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熊磊
兰道松
梁红波
黄圣梅
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Jiangxi Guoji Nano Science And Technology Co ltd
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Nanchang Hangkong University
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/687—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing atoms other than phosphorus, silicon, sulfur, nitrogen, oxygen or carbon in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
    • C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C08K7/06—Elements
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08K9/00—Use of pretreated ingredients
    • C08K9/10—Encapsulated ingredients
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/40—Fibres of carbon

Abstract

The invention discloses a method for preparing polythioether polymer grafted carbon fibers on the basis of thiol-ene photopolymerization. The method specifically includes the steps that firstly, carbon fibers are subjected to acidification to obtain acidified carbon fibers; secondly, the acidified carbon fibers further react with mercapto-alcohol to obtain sulfhydrylated carbon fibers; thirdly, the sulfhydrylated carbon fibers, dimercapto monomers and diene monomers initiate a thiol-ene photopolymerization reaction under irradiation of ultraviolet, and the polythioether polymer grafted carbon fibers are obtained. The method has the advantages that by means of the thiol-ene photopolymerization reaction, the consumption of solvents is reduced, after-treatment steps are simplified, large-scale production is benefited, and meanwhile the toxic and harmful acylating chlorination process existing in a traditional carbon fiber surface grafting and modifying process is avoided; polythioether polymer is grafted on the surfaces of the carbon fibers so that active functional groups on the surfaces of the carbon fibers are increased, wettability of the carbon fibers with resin is easily improved, and interface performance between the carbon fibers and a resin matrix is improved.

Description

A kind of polysulfide polymers based on sulfydryl-alkene photopolymerization are grafted the preparation of carbon fiber Method
Technical field
The present invention relates to a kind of polysulfide polymers based on sulfydryl-alkene photopolymerization are grafted the preparation method of carbon fiber.
Background technology
Carbon fiber enhancement resin base composite material as a kind of important structural material of aerospace field, because with high ratio The advantages of intensity, high ratio modulus, high temperature resistant, designability are good and corrosion-resistant, causes people widely to pay close attention in recent years.But not The carbon fiber surface of Jing process is inert and active function groups are less, poor with the wellability of resin matrix, causes itself and resin The interface cohesion of matrix is poor, and interface has more defect, which has limited carbon fiber enhancement resin base composite material globality The performance of energy.Therefore, to carbon fiber surface modification to improve its binding ability between resin matrix, it is that current carbon fiber is multiple One of emphasis of condensation material research field.
Have at many kinds, including oxidation processes, cladding process and radiation currently for the surface modifying method of carbon fiber Reason etc., but these method processing procedures are more complicated, and modification efficiency is not high, and some modifying process even can produce harmful substance.And Sulfydryl-alkene light polymerization method is received much concern in recent years as a kind of new inorganic material surface graft-modification method, and it is click on One kind in chemical method, can complete various chemical syntheses fast and reliablely by the splicing of junior unit.It has range of application Extensively, the advantages of yield is high, accessory substance is harmless, reaction condition is simple, reaction speed is fast.
It is based on probing into carbon fiber surface modification method, poly- in carbon fiber surface grafting using sulfydryl-alkene light polymerization method Disulfide polymer.Light trigger is added in course of reaction, reaction is completed under ultraviolet light, its reaction condition is more gentle, Solvent usage amount is low, and accessory substance is few, and preparation process is simple, and the time is very short, is very beneficial for popularization and application aborning.Carbon is fine After grafting polysulfide polymers, its surface can introduce substantial amounts of active function groups to dimension, and surface-active is improved, and can be effectively improved carbon Interfacial combined function between fiber and resin matrix.
The content of the invention
It is an object of the invention to provide one kind that a kind of experimental procedure is simple, the reaction time is short is poly- based on sulfydryl-alkene light The polysulfide polymers of conjunction are grafted the preparation method of carbon fiber, and being mainly characterized by of the method is existed using sulfydryl-alkene light polymerization method Carbon fiber surface is grafted polysulfide polymers, and reaction time is shorter, yield is high, accessory substance is few and harmless, and be modified resulting carbon Fiber surface wraps up one layer of polysulfide polymers containing active group, can be effectively improved the infiltration of carbon fiber and resin matrix Property, improve the interaction between carbon fiber and matrix.
The present invention is achieved like this, a kind of polysulfide polymers grafting carbon fiber based on sulfydryl-alkene photopolymerization Preparation method, is characterized in that method and step is：
The first step：1g original carbon fibers are added in the red fuming nitric acid (RFNA) that 50～100mL mass percent concentrations are 65%, 70～ At 100 DEG C, back flow reaction 2～6 hours, it is neutral that reaction is cleaned with distilled water after terminating to pH value, is placed in 80 DEG C of vacuum drying It is dried 24 hours in case, you can obtain acid treatment carbon fiber；
Second step：0.5g acid treatments carbon fiber and 0.01 ~ 0.1 mole of mercaptoalcohol are added in 20 ~ 50mL dimethylbenzene, under room temperature Stirring adds 0.001 ~ 0.01 mole of DMAP and 0.01 ~ 0.1 mole of dicyclohexyl carbon two after 30 ~ 50 minutes Imines, continues reaction 4 ~ 8 hours under room temperature, reaction terminates rear suction filtration and cleaned with dimethylbenzene 4 times, is subsequently placed in 80 DEG C of vacuum and does It is dried 24 hours in dry case, you can obtain sulfhydrylation carbon fiber；
3rd step：By the diene list of 0.5g sulfhydrylation carbon fibers, 0.01 ~ 0.2 mole of dimercapto monomer and 0.01 ~ 0.2 mole Body is added in the dimethylformamide of 20 ~ 50mL, is subsequently adding the light trigger of 10 ~ 100mg, adopts wavelength for 365nm's Ultraviolet light trigger monomer photopolymerization in 10 ~ 30 minutes, reaction terminate rear suction filtration and are cleaned with dichloromethane 4 times, true at 80 DEG C It is dried 24 hours in empty drying box, you can obtain polysulfide polymers grafting carbon fiber.
Described mercaptoalcohol is the one kind in mercaptoethanol, 3- sulfydryl -1- propyl alcohol or 4- sulfydryls-n-butyl alcohol.
Described dimercapto monomer is 1,2- dithioglycols, 1,3- dimercaptopropanes, penta 2 sulphur of Isosorbide-5-Nitrae-succinimide mercaptans or 1,5- One kind of alcohol.
Described diene monomers be diethylene glycol divinyl ether, divinyl ether, diallyl ether, 1,3-butadiene or One kind in Isosorbide-5-Nitrae-pentadiene.
Described light trigger is benzoin dimethylether or the one kind in 2- hydroxy-2-methyl -1- phenyl -1- acetone.
The present invention has advantages below：The present invention solves carbon fiber surface inertia, and surface-active functional group is few, with resin The problems such as matrix wellability and interface cohesion difference.By sulfydryl-alkene photopolymerization reaction, solvent load is reduced, after simplifying Process step, is conducive to large-scale production, while existing during avoiding traditional carbon fibres surface graft modification virulent Chloride process, increases can its surface-active functional group by being grafted polysulfide polymers in carbon fiber surface, be conducive to carrying High its wellability with resin, improves the interface performance between carbon fiber and resin matrix.
Specific embodiment
Embodiment 1:
This example demonstrates that a kind of polysulfide polymers based on sulfydryl-alkene photopolymerization that the present invention is provided are grafted the system of carbon fiber Preparation Method.
The first step：1g original carbon fibers are added in the red fuming nitric acid (RFNA) that 70mL mass percent concentrations are 65%, at 90 DEG C Under, back flow reaction 4 hours, it is neutral that reaction is cleaned with distilled water after terminating to pH value, is placed in 80 DEG C of vacuum drying chambers and is dried 24 hours, you can obtain acid treatment carbon fiber；
Second step：0.5g acid treatments carbon fiber and 0.05 mole of 3- sulfydryl -1- propyl alcohol are added in 40mL dimethylbenzene, under room temperature Stirring adds 0.005 mole of DMAP and 0.05 mole of dicyclohexylcarbodiimide after 40 minutes, under room temperature Continue reaction 6 hours, reaction terminates rear suction filtration and cleaned with dimethylbenzene 4 times, in being subsequently placed in 80 DEG C of vacuum drying chambers, be dried 24 Hour, you can obtain sulfhydrylation carbon fiber；
3rd step：The divinyl ether of 0.5g sulfhydrylation carbon fibers, 0.1 mole of 1,3- dimercaptopropanes and 0.1 mole is added To in the dimethylformamide of 40mL, be subsequently adding the benzoin dimethylether of 20mg, adopt wavelength for 365nm ultraviolet light Trigger monomer photopolymerization in 15 minutes, reaction terminate rear suction filtration and are cleaned with dichloromethane 4 times, are dried in 80 DEG C of vacuum drying chambers 24 hours, you can obtain polysulfide polymers grafting carbon fiber.
Embodiment 2:
This example demonstrates that a kind of polysulfide polymers based on sulfydryl-alkene photopolymerization that the present invention is provided are grafted the system of carbon fiber Preparation Method.
The first step：1g original carbon fibers are added in the red fuming nitric acid (RFNA) that 50mL mass percent concentrations are 65%, at 70 DEG C Under, back flow reaction 6 hours, it is neutral that reaction is cleaned with distilled water after terminating to pH value, is placed in 80 DEG C of vacuum drying chambers and is dried 24 hours, you can obtain acid treatment carbon fiber；
Second step：0.5g acid treatments carbon fiber and 0.01 mole of 4- sulfydryls-n-butyl alcohol are added in 20mL dimethylbenzene, under room temperature Stirring adds 0.001 mole of DMAP and 0.01 mole of dicyclohexylcarbodiimide after 30 minutes, under room temperature Continue reaction 4 hours, reaction terminates rear suction filtration and cleaned with dimethylbenzene 4 times, in being subsequently placed in 80 DEG C of vacuum drying chambers, be dried 24 Hour, you can obtain sulfhydrylation carbon fiber；
3rd step：By the diethylene glycol diethyl of 0.5g sulfhydrylation carbon fibers, 0.01 mole of 1,5- pentane disulfide thioalcohols and 0.01 mole Alkene ether is added in the dimethylformamide of 20mL, is subsequently adding the benzoin dimethylether of 10mg, adopts wavelength for 365nm's Ultraviolet light trigger monomer photopolymerization in 30 minutes, reaction terminate rear suction filtration and are cleaned with dichloromethane 4 times, dry in 80 DEG C of vacuum It is dried 24 hours in dry case, you can obtain polysulfide polymers grafting carbon fiber.
Embodiment 3:
The first step：1g original carbon fibers are added in the red fuming nitric acid (RFNA) that 100mL mass percent concentrations are 65%, at 100 DEG C, Back flow reaction 2 hours, it is neutral that reaction is cleaned with distilled water after terminating to pH value, is placed in 80 DEG C of vacuum drying chambers dry 24 little When, you can obtain acid treatment carbon fiber；
Second step：0.5g acid treatments carbon fiber and 0.1 mole of mercaptoethanol are added in 50mL dimethylbenzene, under room temperature, 50 is stirred 0.01 mole of DMAP and 0.1 mole of dicyclohexylcarbodiimide are added after minute, under room temperature, continues reaction 8 Hour, reaction terminates rear suction filtration and is cleaned with dimethylbenzene 4 times, is dried 24 hours in being subsequently placed in 80 DEG C of vacuum drying chambers, you can Obtain sulfhydrylation carbon fiber；
3rd step：The 1,3-butadiene of 0.5g sulfhydrylation carbon fibers, 0.2 mole of 1,2- dithioglycols and 0.2 mole is added To in the dimethylformamide of 50mL, be subsequently adding the 2- hydroxy-2-methyl -1- phenyl -1- acetone of 100mg, adopt wavelength for The ultraviolet light trigger monomer photopolymerization in 10 minutes of 365nm, reaction terminate rear suction filtration and are cleaned with dichloromethane 4 times, 80 It is dried 24 hours in DEG C vacuum drying chamber, you can obtain polysulfide polymers grafting carbon fiber.

Claims (5)

1. a kind of polysulfide polymers based on sulfydryl-alkene photopolymerization are grafted the preparation method of carbon fiber, and its feature is described Method is comprised the following steps：
The first step：1g original carbon fibers are added in the red fuming nitric acid (RFNA) that 50～100mL mass percent concentrations are 65%, 70～ At 100 DEG C, back flow reaction 2～6 hours, it is neutral that reaction is cleaned with distilled water after terminating to pH value, is placed in 80 DEG C of vacuum drying It is dried 24 hours in case, you can obtain acid treatment carbon fiber；
Second step：0.5g acid treatments carbon fiber and 0.01 ~ 0.1 mole of mercaptoalcohol are added in 20 ~ 50mL dimethylbenzene, under room temperature Stirring adds 0.001 ~ 0.01 mole of DMAP and 0.01 ~ 0.1 mole of dicyclohexyl carbon two after 30 ~ 50 minutes Imines, continues reaction 4 ~ 8 hours under room temperature, reaction terminates rear suction filtration and cleaned with dimethylbenzene 4 times, is subsequently placed in 80 DEG C of vacuum and does It is dried 24 hours in dry case, you can obtain sulfhydrylation carbon fiber；
3rd step：By the diene list of 0.5g sulfhydrylation carbon fibers, 0.01 ~ 0.2 mole of dimercapto monomer and 0.01 ~ 0.2 mole Body is added in the dimethylformamide of 20 ~ 50mL, is subsequently adding the light trigger of 10 ~ 100mg, adopts wavelength for 365nm's Ultraviolet light trigger monomer photopolymerization in 10 ~ 30 minutes, reaction terminate rear suction filtration and are cleaned with dichloromethane 4 times, true at 80 DEG C It is dried 24 hours in empty drying box, you can obtain polysulfide polymers grafting carbon fiber.
2. a kind of polysulfide polymers based on sulfydryl-alkene photopolymerization as claimed in claim 1 are grafted the preparation side of carbon fiber Method, it is characterised in that described mercaptoalcohol is the one kind in mercaptoethanol, 3- sulfydryl -1- propyl alcohol or 4- sulfydryls-n-butyl alcohol.
3. a kind of polysulfide polymers based on sulfydryl-alkene photopolymerization as claimed in claim 1 are grafted the preparation side of carbon fiber Method, it is characterised in that described dimercapto monomer is 1,2- dithioglycols, 1,3- dimercaptopropanes, Isosorbide-5-Nitrae-succinimide mercaptans or 1,5- penta One kind of two mercaptan.
4. a kind of polysulfide polymers based on sulfydryl-alkene photopolymerization as claimed in claim 1 are grafted the preparation side of carbon fiber Method, it is characterised in that described diene monomers are diethylene glycol divinyl ether, divinyl ether, diallyl ether, 1,3- fourths One kind in diene or Isosorbide-5-Nitrae-pentadiene.
5. a kind of polysulfide polymers based on sulfydryl-alkene photopolymerization as claimed in claim 1 are grafted the preparation side of carbon fiber Method, it is characterised in that described light trigger is in benzoin dimethylether or 2- hydroxy-2-methyl -1- phenyl -1- acetone Kind.
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CN109577007A (en) * 2018-11-15 2019-04-05 南昌航空大学 A kind of preparation method of hyper-branched polyester grafting carbon fiber
CN112080147A (en) * 2020-09-18 2020-12-15 宁波工程学院 Preparation method of sulfydryl organic silicon nanospheres and sulfydryl-alkene polymer flame-retardant system thereof
CN115703892A (en) * 2021-08-09 2023-02-17 中南民族大学 High-performance degradable epoxy resin-carbon fiber composite material and preparation method thereof

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CN112080147B (en) * 2020-09-18 2023-03-31 宁波工程学院 Preparation method of sulfydryl organic silicon nanospheres and sulfydryl-alkene polymer flame-retardant system thereof
CN115703892A (en) * 2021-08-09 2023-02-17 中南民族大学 High-performance degradable epoxy resin-carbon fiber composite material and preparation method thereof

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