CN106521970B - A kind of preparation method based on sulfydryl-alkene photopolymerization polysulfide polymers grafting carbon fiber - Google Patents
A kind of preparation method based on sulfydryl-alkene photopolymerization polysulfide polymers grafting carbon fiber Download PDFInfo
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- CN106521970B CN106521970B CN201610965271.XA CN201610965271A CN106521970B CN 106521970 B CN106521970 B CN 106521970B CN 201610965271 A CN201610965271 A CN 201610965271A CN 106521970 B CN106521970 B CN 106521970B
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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
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- 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
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- 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
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- 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
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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
- 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 kind of preparation methods based on sulfydryl-alkene photopolymerization polysulfide polymers grafting carbon fiber.Specific steps are as follows: carbon fiber is subjected to acidification first, obtains acidification carbon fiber；It further reacts to obtain sulfhydrylation carbon fiber with mercaptoalcohol；Again this sulfhydrylation carbon fiber and dimercapto monomer, diene monomers are caused into sulfydryl-alkene photopolymerization reaction under ultraviolet lighting, obtains polysulfide polymers grafting carbon fiber.The invention has the following advantages that passing through sulfydryl-alkene photopolymerization reaction; reduce solvent usage; simplify post-processing step; be conducive to large-scale production; avoiding traditional carbon fibres surface graft modification simultaneously, there are toxic chloride processes in the process; its surface-active functional group can be made to increase by being grafted polysulfide polymers in carbon fiber surface, be conducive to the wellability for improving it with resin, improve the interface performance between carbon fiber and resin matrix.
Description
Technical field
The present invention relates to a kind of preparation methods based on sulfydryl-alkene photopolymerization polysulfide polymers grafting carbon fiber.
Background technique
Carbon fiber enhancement resin base composite material is as a kind of important structural material of aerospace field, because having high ratio
The advantages that 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
Processed carbon fiber surface is inert and active function groups are less, poor with the wellability of resin matrix, leads to itself and resin
The interface cohesion of matrix is poor, and there are more defects for interface, and which has limited carbon fiber enhancement resin base composite material globalities
The performance of energy.It therefore, is that current carbon fiber is multiple to carbon fiber surface modification to improve its binding performance between resin matrix
One of the emphasis of condensation material research field.
There are many kinds of the surface modifying methods for being directed to carbon fiber at present, including at oxidation processes, cladding processing and radiation
Reason etc., but these method treatment processes are more complex, and modification efficiency is not high, and some modifying process even can generate harmful substance.And
Sulfydryl-alkene light polymerization method is concerned in recent years as a kind of novel inorganic material surface graft-modification method, it is to click
One of chemical method can complete fast and reliablely various chemical syntheses by the splicing of junior unit.It has application range
Extensively, the advantages that yield is high, by-product is harmless, reaction condition is simple, reaction speed is fast.
Based on probing into carbon fiber surface modification method, it is grafted and is gathered in carbon fiber surface using sulfydryl-alkene light polymerization method
Disulfide polymer.Photoinitiator is added in reaction process, reaction is completed under ultraviolet light, reaction condition is more mild,
Solvent usage amount is low, and by-product is few, and preparation process is simple, and the time is very short, is very beneficial for promoting and applying in production.Carbon fiber
For dimension after being grafted polysulfide polymers, surface can introduce a large amount of active function groups, and surface-active improves, and can effectively improve carbon
Interfacial combined function between fiber and resin matrix.
Summary of the invention
The purpose of the present invention is to provide a kind of experimental procedures, and one kind simple, that the reaction time is short is poly- based on sulfydryl-alkene light
The preparation method of the polysulfide polymers grafting carbon fiber of conjunction, the method are mainly characterized by existing using sulfydryl-alkene light polymerization method
Carbon fiber surface is grafted polysulfide polymers, and reaction time is shorter, yield is high, by-product is few and harmless, modified obtained 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 to be grafted carbon fiber based on sulfydryl-alkene photopolymerization polysulfide polymers
Preparation method, it is characterized in that method and step are as follows:
Step 1: 1g original carbon fiber is added in the concentrated nitric acid that 50~100mL mass percent concentration is 65%,
At 70~100 DEG C, back flow reaction 2~6 hours, after reaction wash with distilled water to pH value be neutrality, be placed in 80 DEG C of vacuum
It is 24 hours dry in drying box, sour Treatment of Carbon can be obtained；
Step 2: 0.5g acid Treatment of Carbon and 0.01 ~ 0.1 mole of mercaptoalcohol are added in 20 ~ 50mL dimethylbenzene, room
0.001 ~ 0.01 mole of 4-dimethylaminopyridine and 0.01 ~ 0.1 mole of dicyclohexyl is added after lower stirring 30 ~ 50 minutes in temperature
Carbodiimide, the reaction was continued at room temperature 4 ~ 8 hours, filters and is cleaned 4 times after reaction with dimethylbenzene, is subsequently placed in 80 DEG C very
It is 24 hours dry in empty drying box, sulfhydrylation carbon fiber can be obtained；
Step 3: by 0.5g sulfhydrylation carbon fiber, 0.01 ~ 0.2 mole of dimercapto monomer and the two of 0.01 ~ 0.2 mole
Alkene monomer is added in the dimethylformamide of 20 ~ 50mL, then be added 10 ~ 100mg photoinitiator, use wavelength for
10 ~ 30 minutes initiation monomer photopolymerizations of ultraviolet light of 365nm are filtered after reaction and are cleaned 4 times with methylene chloride,
It is 24 hours dry in 80 DEG C of vacuum ovens, polysulfide polymers grafting carbon fiber can be obtained.
The mercaptoalcohol is one of mercaptoethanol, 3- sulfydryl -1- propyl alcohol or 4- sulfydryl-n-butyl alcohol.
The dimercapto monomer is 1,2- dithioglycol, 1,3- dimercaptopropane, Isosorbide-5-Nitrae-succinimide mercaptans or 1, penta 2 sulphur of 5-
One kind of alcohol.
The diene monomers be diethylene glycol divinyl ether, divinyl ether, diallyl ether, 1,3-butadiene or
One of Isosorbide-5-Nitrae-pentadiene.
The photoinitiator is one of benzoin dimethylether or 2- hydroxy-2-methyl -1- phenyl -1- acetone.
The invention has the following advantages that the present invention solves carbon fiber surface inertia, surface-active functional group is few, with resin
The problems such as matrix infiltration and poor interface cohesion.By sulfydryl-alkene photopolymerization reaction, reduce solvent usage, after simplifying
Processing step is conducive to large-scale production, while avoiding during traditional carbon fibres surface graft modification that there are toxic
Chloride process can be such that its surface-active functional group increases, be conducive to mention by being grafted polysulfide polymers in carbon fiber surface
The wellability of high itself and resin, improves the interface performance between carbon fiber and resin matrix.
Specific embodiment
Embodiment 1:
This example demonstrates that provided by the invention a kind of based on sulfydryl-alkene photopolymerization polysulfide polymers grafting carbon fiber
Preparation method.
Step 1: 1g original carbon fiber is added in the concentrated nitric acid that 70mL mass percent concentration is 65%, at 90 DEG C
Under, back flow reaction 4 hours, to pH value it is wash with distilled water after reaction neutrality, is placed in 80 DEG C of vacuum ovens dry
24 hours, sour Treatment of Carbon can be obtained；
Step 2: 0.5g acid Treatment of Carbon and 0.05 mole of 3- sulfydryl -1- propyl alcohol are added in 40mL dimethylbenzene, room
0.005 mole of 4-dimethylaminopyridine and 0.05 mole of dicyclohexylcarbodiimide, room is added in the lower stirring of temperature after forty minutes
Temperature is lower, and the reaction was continued 6 hours, filters and is cleaned 4 times after reaction with dimethylbenzene, is subsequently placed in 80 DEG C of vacuum ovens and does
Dry 24 hours, sulfhydrylation carbon fiber can be obtained；
Step 3: by 0.5g sulfhydrylation carbon fiber, 0.1 mole of 1,3- dimercaptopropane and 0.1 mole of divinyl ether
It is added in the dimethylformamide of 40mL, the benzoin dimethylether of 20mg is then added, uses wavelength for the ultraviolet light of 365nm
15 minutes initiation monomer photopolymerizations are irradiated, filter after reaction and are cleaned 4 times with methylene chloride, in 80 DEG C of vacuum ovens
It is 24 hours dry, polysulfide polymers grafting carbon fiber can be obtained.
Embodiment 2:
This example demonstrates that provided by the invention a kind of based on sulfydryl-alkene photopolymerization polysulfide polymers grafting carbon fiber
Preparation method.
Step 1: 1g original carbon fiber is added in the concentrated nitric acid that 50mL mass percent concentration is 65%, at 70 DEG C
Under, back flow reaction 6 hours, to pH value it is wash with distilled water after reaction neutrality, is placed in 80 DEG C of vacuum ovens dry
24 hours, sour Treatment of Carbon can be obtained；
Step 2: 0.5g acid Treatment of Carbon and 0.01 mole of 4- sulfydryl-n-butyl alcohol are added in 20mL dimethylbenzene, room
0.001 mole of 4-dimethylaminopyridine and 0.01 mole of dicyclohexylcarbodiimide, room is added after lower stirring 30 minutes in temperature
Temperature is lower, and the reaction was continued 4 hours, filters and is cleaned 4 times after reaction with dimethylbenzene, is subsequently placed in 80 DEG C of vacuum ovens and does
Dry 24 hours, sulfhydrylation carbon fiber can be obtained；
Step 3: by 0.5g sulfhydrylation carbon fiber, 0.01 mole of 1,5- pentane disulfide thioalcohol and 0.01 mole of diethylene glycol
Divinyl ether is added in the dimethylformamide of 20mL, then be added 10mg benzoin dimethylether, use wavelength for
30 minutes initiation monomer photopolymerizations of ultraviolet light of 365nm are filtered and are cleaned 4 times with methylene chloride, after reaction 80
It is 24 hours dry in DEG C vacuum oven, polysulfide polymers grafting carbon fiber can be obtained.
Embodiment 3:
Step 1: 1g original carbon fiber is added in the concentrated nitric acid that 100mL mass percent concentration is 65%, at 100 DEG C
Under, back flow reaction 2 hours, to pH value it is wash with distilled water after reaction neutrality, is placed in 80 DEG C of vacuum ovens dry
24 hours, sour Treatment of Carbon can be obtained；
Step 2: 0.5g acid Treatment of Carbon and 0.1 mole of mercaptoethanol are added in 50mL dimethylbenzene, stir at room temperature
0.01 mole of 4-dimethylaminopyridine and 0.1 mole of dicyclohexylcarbodiimide are added after mixing 50 minutes, continues at room temperature
Reaction 8 hours is filtered after reaction and is cleaned 4 times with dimethylbenzene, is subsequently placed in drying 24 hours in 80 DEG C of vacuum ovens,
Sulfhydrylation carbon fiber can be obtained；
Step 3: by 0.5g sulfhydrylation carbon fiber, 0.2 mole of 1,2- dithioglycol and 0.2 mole of 1,3-butadiene
It is added in the dimethylformamide of 50mL, the 2- hydroxy-2-methyl -1- phenyl -1- acetone of 100mg is then added, using wave
10 minutes initiation monomer photopolymerizations of ultraviolet light of a length of 365nm are filtered after reaction and are cleaned 4 times with methylene chloride,
It is 24 hours dry in 80 DEG C of vacuum ovens, polysulfide polymers grafting carbon fiber can be obtained.
Claims (5)
1. a kind of preparation method based on sulfydryl-alkene photopolymerization polysulfide polymers grafting carbon fiber, it is characterized in that described
Method the following steps are included:
Step 1: 1g original carbon fiber is added in the concentrated nitric acid that 50~100mL mass percent concentration is 65%, 70~
At 100 DEG C, back flow reaction 2~6 hours, after reaction wash with distilled water to pH value be neutrality, be placed in 80 DEG C of vacuum drying
It is 24 hours dry in case, sour Treatment of Carbon can be obtained；
Step 2: 0.5g acid Treatment of Carbon and 0.01 ~ 0.1 mole of mercaptoalcohol are added in 20 ~ 50mL dimethylbenzene, at room temperature
0.001 ~ 0.01 mole of 4-dimethylaminopyridine and 0.01 ~ 0.1 mole of dicyclohexyl carbon two is added after stirring 30 ~ 50 minutes
Imines, the reaction was continued at room temperature 4 ~ 8 hours, filters and is cleaned 4 times after reaction with dimethylbenzene, and it is dry to be subsequently placed in 80 DEG C of vacuum
It is 24 hours dry in dry case, sulfhydrylation carbon fiber can be obtained；
Step 3: by 0.5g sulfhydrylation carbon fiber, 0.01 ~ 0.2 mole of dimercapto monomer and 0.01 ~ 0.2 mole of diene list
Body is added in the dimethylformamide of 20 ~ 50mL, and the photoinitiator of 10 ~ 100mg is then added, uses wavelength for 365nm's
10 ~ 30 minutes initiation monomer photopolymerizations of ultraviolet light are filtered after reaction and are cleaned 4 times with methylene chloride, true at 80 DEG C
It is 24 hours dry in empty drying box, polysulfide polymers grafting carbon fiber can be obtained.
2. a kind of preparation side based on sulfydryl-alkene photopolymerization polysulfide polymers grafting carbon fiber as described in claim 1
Method, it is characterised in that the mercaptoalcohol is one of mercaptoethanol, 3- sulfydryl -1- propyl alcohol or 4- sulfydryl-n-butyl alcohol.
3. a kind of preparation side based on sulfydryl-alkene photopolymerization polysulfide polymers grafting carbon fiber as described in claim 1
Method, it is characterised in that the dimercapto monomer is 1,2- dithioglycol, 1,3- dimercaptopropane, Isosorbide-5-Nitrae-succinimide mercaptans or 1,5- penta
One kind of two mercaptan.
4. a kind of preparation side based on sulfydryl-alkene photopolymerization polysulfide polymers grafting carbon fiber as described in claim 1
Method, it is characterised in that the diene monomers are diethylene glycol divinyl ether, divinyl ether, diallyl ether, 1,3- fourth
One of diene or Isosorbide-5-Nitrae-pentadiene.
5. a kind of preparation side based on sulfydryl-alkene photopolymerization polysulfide polymers grafting carbon fiber as described in claim 1
Method, it is characterised in that the photoinitiator is one in benzoin dimethylether or 2- hydroxy-2-methyl -1- phenyl -1- acetone
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| CN109577007B (en) * | 2018-11-15 | 2021-04-09 | 南昌航空大学 | Preparation method of hyperbranched polyester grafted carbon fiber |
| CN109575287A (en) * | 2018-11-15 | 2019-04-05 | 南昌航空大学 | A method of dissaving polymer/carbon nanotube/carbon fiber spans scale reinforcement is prepared based on sulfydryl-alkene click-reaction |
| 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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